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This package is built for early-stage founders who are wanting to accelerate their path to building a successful startup with help from an experienced founder. Whether you're pre-launch, post-MVP, or in the middle of raising a round, this coaching plan is designed to meet you where you are—and help you go further, faster. You’ll work 1-on-1 with an experienced founder or operator to refine your strategy, overcome blockers, and build a company with real momentum. Available in 5- or 10-hour formats, this flexible package gives you high-leverage support across your most critical areas—from fundraising and GTM to team building and founder mindset. Common coaching activities include: - Fundraising Strategy & Pitch Feedback: Craft your story, build your deck, and prep for investor conversations. - Go-to-Market Planning: Validate your ICP, test channels, and drive early traction. - Product & Roadmap Feedback: Prioritize what to build (and what not to), based on real customer feedback. - Growth Experiments & Funnels: Design scrappy experiments to drive activation, retention, and conversion. - Hiring & Team Building: Recruit and retain early team members who raise the bar. - Founder Mindset & Focus: Manage stress, avoid burnout, and stay focused on what matters most. - Investor Updates & Board Management: Learn how to communicate clearly, build trust, and stay in control of your narrative. - Pricing, Packaging, and GTM Strategy: Get feedback on your model and position it to win. Each session is personalized to your needs—whether you’re trying to close your first 10 customers, raise a $5M seed round, or navigate early team dynamics. You’ll walk away with clarity, momentum, and a real partner in your corner.
Clearer strategy across product, GTM, and fundraising
Sharper investor pitch and more compelling story
Confidence navigating uncertainty and high-stakes choices
Support system to avoid burnout and stay focused
Actionable advice tailored to your unique stage and goals
Stronger founder narrative for customers, hires, and investors
Feedback on deck, metrics, pricing, and product roadmap
Trusted founder/operator in your corner when it matters most
Coaching delivered via live sessions and .
Services included:
Ideation
Compensation Strategy
Hiring
Fundraising
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
Get help with Ideation, Business Strategy Development, and .
Jonathan also coaches for Venture Capital and Climate Tech & Sustainability. View all.

Joined June 2026
$300M Raised. 30+ Startups Backed. Ex-Founder, VC and Head of IR
I've spent my career on both sides of the table, which gives me a unique vantage point on what actually makes a founder fundable. I started at THRIVE, an award-winning early-stage accelerator focused on agtech, where I worked hands-on with founders from idea to fundable company — meaning I've sat across the table from hundreds of pitches and seen exactly what separates the ones that land from the ones that don't. That experience led me into venture investing at Scrum Ventures, where I invested across food, deep tech, healthcare, AI, and other sectors, and progressed from Associate to Principal in two years — time spent in IC meetings hearing how partners actually argue for or against a deal. Two of my portfolio bets show what a well-told story and a fundable business can produce together: one company exited for nine figures to a publicly traded acquirer, and another has since become a unicorn generating billions in annual revenue. From there, I moved to the operator side at GrubMarket, a pre-IPO food-tech unicorn, where I built the company's investor relations function from scratch — orchestrating nearly $300M across multiple rounds and becoming the company's public-facing voice with over 100 investors and stakeholders. Today, as a Venture Partner at Scrum, I continue advising portfolio companies on fundraising strategy, which keeps me current on how deals actually get sourced, evaluated, and won — not from theory, but from sitting in the room. If you're preparing to raise, I can help with every part of it — refining your narrative so it resonates with the specific investors you're targeting, building a deck and data room that holds up under real diligence, and coaching you through the investor meetings themselves so you walk in prepared rather than reactive. I can also help you think like the person across the table: what actually gets a deal through an investment committee, what diligence questions are coming and why, and how to keep investors engaged and informed long after the round closes through real IR practice. This isn't secondhand advice — it's the exact process I've lived on both sides, from coaching founders pre-fundability at THRIVE, to deciding which bets to make at Scrum, to running IR for a company that raised nearly $300M of its own.
5h+ of coaching